


Pillow Talk

by AnaliseGrey



Category: Critical Role (Web Series)
Genre: (I know it's a shock), Alternate Universe - Modern Setting, Anal Sex, Begging, Dom Caleb Widogast, M/M, Nipple Clamps, Rope Bondage, Sub Mollymauk Tealeaf, sexy challenges, this fic has embedded art!, yet more smut
Language: English
Status: Completed
Published: 2021-01-17
Updated: 2021-01-17
Packaged: 2021-03-15 01:29:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,544
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28805094
Author URL: https://archiveofourown.org/users/AnaliseGrey/pseuds/AnaliseGrey
Summary: "Mollymauk-""No- Caleb, please, I'm almost- I'm so close-""Time is up,schatz. You know what that means."Molly whines, hips still moving, desperately trying to rut against the softened memory foam of his pillow, but it only gives-way under the pressure rather than providing the resistance he wants, the friction he needs.There's movement behind him, and the clamps at his nipples tug viciously as Caleb pulls his tail backwards. He can try to resist, but he knows that ultimately all it will get him is sore nipples, so he moves with it, whimpering as the head of his cock brushes the pillow on his way off it.Caleb lays him out again, bound hands pressed up near the headboard, just before Caleb leans over him with a smile."Just a short while for it to cool and firm up again,liebling. Don’t worry, though. I will help keep you occupied while we wait."
Relationships: Mollymauk Tealeaf/Caleb Widogast
Comments: 10
Kudos: 142





	Pillow Talk

**Author's Note:**

> Special thanks to [ChinCHILLaArts](http://chinchillaarts.tumblr.com/) for the art which sparked the idea for this in the first place (which, coincidentally, can be found embedded within the fic!).
> 
> It was _very_ inspiring.

"Mollymauk-"

" _No_ \- Caleb, please, I'm almost- I'm so close-"

"Time is up, _schatz_. You know what that means."

Molly whines, hips still moving, desperately trying to rut against the softened memory foam of his pillow, but it only gives-way under the pressure rather than providing the resistance he wants, the friction he needs.

There's movement behind him, and the clamps at his nipples tug viciously as Caleb pulls his tail backwards. He can try to resist, but he knows that ultimately all it will get him is sore nipples, so he moves with it, whimpering as the head of his cock brushes the pillow on his way off it.

Caleb lays him out again, bound hands pressed up near the headboard, just before Caleb leans over him with a smile.

"Just a short while for it to cool and firm up again, _liebling_. Don’t worry, though. I will help keep you occupied while we wait."

“I just bet you will- _aaa_!” Molly jolts as Caleb raises an eyebrow and tugs sharply on one of the leads from the band on his tail to the clover clamps on his nipples.

“I can keep you occupied pleasantly,” Caleb says, free hand brushing light fingertips over Molly’s cock, making him whine and buck. “Or not-so-pleasantly.” He tugs at the clamp lead again, and Molly whimpers, squirming.

“Pleasant! Pleasant, please, Caleb.”

“I thought you might say that.” Caleb lets go of the clamp lead and Molly breathes a sigh of relief.

His relief doesn’t last long as Caleb wriggles down until he’s settled between Molly’s legs, one hand holding the base of Molly’s cock to point it towards himself.

“Eyes on me, _schatz_.”

Molly lets out another whimper before forcing his eyes open and gaze downward until he’s meeting Caleb’s eyes.

“Very good.”

With that, Caleb starts teasing, flicking his tongue in tiny licks over and around the head of Molly’s cock. Molly wants to writhe, to move, to throw his head back and groan, but he knows if he looks away, Caleb will stop. So instead he forces himself still, makes himself keep watching as Caleb takes him apart with the smallest movements of his tongue.

Fifteen minutes. He has to suffer this for fifteen minutes. Molly knows this because Caleb helpfully told him so; Caleb’s very precise that way.

‘ _You will have five minutes from the time you get on the pillow to make yourself come. After five minutes the foam is too soft, and it won’t work. I will then keep you occupied for the fifteen minutes it needs to firm up again as it cools off._ ’

‘Occupied’, Caleb said. ‘Torture Molly to the bounds of his sanity’, more like.

It doesn’t take him long to start begging, pleading with Caleb to just finish him off, that he’s perfectly fine with a blowjob, it doesn’t need to be fancy. Caleb just holds eye contact before sucking the head of Molly’s dick into his mouth and starting to hum.

It’s like sparks up his spine, but it’s not enough. It’s _not enough_ , and Caleb fucking knows it, the bastard.

“Caleb- Caleb please, I’m begging you- I’ll blow you, let you fuck me, whatever you want, just- _please_.”  
  
Pulling off Molly’s cock with an obscene pop, Caleb looks up at him with a fond smile. He shouldn’t be able to look so sweet and loving while driving Molly out of his damned mind; it’s unfair. 

“ _Schatz_ , you would do all that anyway.”

“I _know_.” Molly whines, squirming as much as he can. “But I’d really, _really_ mean it.”

“I will remind you,” Caleb says, smile widening into a grin. “That this particular game was _your_ idea. That you would come on the pillow or not at all. Are you admitting defeat already?”

“No,” Molly grits out. The idea of being this wound up and not getting to come is unfathomable.

“Just a few more minutes, _schatz_. You can last that long, _ja_?”

“ _Caleb-_ ”

“ _Molly_?” Caleb is still grinning, and it would be infuriating if it weren’t so fucking attractive.

Molly growls something unkind under his breath, but then nods. “Yeah. Yeah, I’ll try.”

“Good boy.” Caleb pats Molly’s thigh, and Molly can’t suppress his shiver at the words.

The next short while feels like forever, stretching like taffy. Having to watch Caleb as he teases him is mean, but in the same same way the clamps are mean. Harmless little cruelties that only make Molly flush and writhe more.

He’s sure this will never end, that he’s going to be stuck forever being teased within an inch of his life when Caleb pulls away, patting Molly’s thigh again.

“Fifteen minutes is up. The pillow should be ready for you now.”

Molly whines, taking a moment to collect himself before bringing his arms back down. Caleb grasps his forearms and helps pull Molly up so he’s sitting on his knees, capturing Molly’s lips in a kiss before Molly can get too far. He wants to touch Caleb so _badly_ , but the ropes at his wrists make it difficult to do much more than scrabble at Caleb’s chest. By the time Caleb releases him again, Molly’s breathless and a bit dazed, as he feels anyone should be after a kiss like that. Caleb moves to the side, gesturing towards the pillow with one hand and patting Molly on the ass with the other.

“Up you go, then.”

Groaning, Molly leverages himself up and moves back to the pillow. Caleb is helpfully holding it up on its side as Molly climbs on, hissing at the coolness against heated skin.

“ _Fuck-_ ” Molly breathes as he settles, immediately widening his knees so he can drop lower and press more-easily into the pillow. His weight makes the middle of the pillow squish down, pushing the end in front of him up and into his dick, making his hips twitch.

This time. Surely this time he’ll manage before the five minutes are up.

He sets himself a brutal pace, rocking his hips, angling to get as much contact with the firmed-up pillow as he can. His tail keeps lashing behind him, tugging randomly at the nipple clamps and all together it’s a delicious torment, knowing he’s so close, that he’s almost there. He has no idea how much longer he’s got- Caleb isn’t counting out loud- and as time passes Molly’s movements get more frenetic, knowing he’s nearing the edge, balls drawing up, heat pooling in his belly. He just needs a few more seconds-

“Mollymauk.”

“ _Please_ , Caleb-”

Caleb puts an arm across the front of Molly’s shoulders and pushes, knocking Molly off the pillow and onto his back. Letting out a frustrated yell, Molly can’t keep his hips from continuing to move even though there’s nothing but air in front of him now. In a fit of frustration he tries to make a grab for his cock himself- it wouldn’t take much- but Caleb grabs the rope at his wrists first and pulls his arms up out of the way.

“Do I need to rebind your hands behind you, _schatz_?”

“ _Caleb_ , please- I need- I’m so close- I can’t wait any longer, ple-”

Caleb leans down and swallows the rest of Molly’s pleas with a kiss. When he pulls back Molly is breathless again, and slightly-less on the edge than he was, more able to think.

That doesn’t mean he’s not _really_ irritated still.

“About your hands, _schatz_?”

Groaning, Molly nods. He isn’t prepared to call his safeword, and he knows he no longer has the will not to touch himself.

“Alright.” Leaning in, Caleb presses a kiss to Molly’s temple. “As I release your hands, you will put them behind you, and I will re-tie them.”

Caleb is thankfully a very deft hand at rope work, and so the process of untying then retying Molly’s wrists is a quick one. To make sure the rope work is solid, Caleb spends a few moments teasing at the head of Molly’s cock with feather-light touches until Molly is begging again, writhing and tugging desperately at his arms. Once Caleb is satisfied, he smiles.

“The pillow should be ready for you.”

Just thinking about it makes Molly’s cock twitch.

Caleb helps a little more this time since Molly’s balance isn’t as good with his arms behind him; climbing up onto the pillow Molly whines. He can’t tell if the pillow keeps getting cooler each time, or if he just keeps getting warmer.

It’s probably him.

For as close as he was when he was stopped before, and how fucking horny Caleb’s teasing has made him, it still takes him a minute or two to really get going. He wants to say he’s never been so hard in his life, but he also knows that he thinks that _every_ time he’s in one of these situations. All the same, the cycling of arousal, denial, calm and building up again have left his dick incredibly sensitive. He swears he can feel the air currents on it, and the drag of heated, sensitive skin over the pillow case is driving him out of his mind.

His ass and thighs are going to be feeling this tomorrow, he knows, and laughs to himself, thinking of all the little old ladies at the yoga studio who ask what his secret for a great ass is. Hips swiveling madly, grinding down as much as he can, and again- he’s so close he can almost taste it, close enough he can feel it gathering behind his eyes and in his belly and almost down to his toes, like lightening or sparklers or-

“ _Schatz-_ ”

“ _No-_ ” Molly cries, eyes scrunched shut, shaking his head side-to-side. “No please, Caleb I can’t- I can’t- _please-_ ”

To his surprise, he isn’t pulled from his perch, and a hand lands on his cheek. He opens his eyes to see Caleb looking at him. Caleb’s thumb swipes across Molly’s cheek, and it’s only then that Molly realizes there are tears of frustration on his face.

“There you are.” Caleb’s lips twitch up into a smile before leaning forward and pressing them to Molly’s, quick and light, before pulling back. “I have a proposition for you.”

Molly snorts.

“You don’t need to proposition me, love. You know I’m a sure thing.”

Giving him a look, Caleb tugs on one of the clamp tethers very lightly, and Molly gasps.

“I have a deal for you, how about that?”

“Yeah, ok-” Molly cuts off in a whine as Caleb gently tugs again. “I would love to hear it, Caleb. Sir. Please.”

“Oh, now you’re polite, I see.” Caleb’s smile curls around his words, and he darts in for another kiss. “If you’ve had enough, and would like to come-”

“ _Yes-_ ” Molly rolls his hips, but the pillow is too soft and it doesn’t get him anywhere. “Yes I do, Caleb, yes-”

“-then what I am going to do is remove the pillow,” Caleb leans in closer, close enough to kiss, but he doesn’t close the last bit of distance. “I am going to tease you for the fifteen minutes you were due, because you did not climb off when I told you to. Then somewhere after that, you’ll get to come.”

“ _Fuck_.”

“Only if you’re very good, _schatz_.”

A shiver zips up Molly’s spine. Good. He can be good; that’s a thing he can do.

“Do you accept?”

“ _Nng_ , yes- yes, Caleb.”

“Alright, then.” Keeping eye contact, Caleb reaches down between them to grasp the pillow, and slowly starts to pull it out from under Molly.

Molly tries to go up on his knees to help, and Caleb pauses. “No, no. Stay where you were.”

A whine pulls out of Molly as the pillow starts to move again, dragging against his balls, parts of the pillowcase barely catching on his cock. As the last of the pillow is between Molly’s thighs, Caleb slows further, the motion of the pillow like molasses. Biting his lip, Molly waits it out, breathing a sigh of relief once the pillow is clear. He goes to bring his legs closer together, to get a more stable position, and Caleb stops him again.

“ _Nein_ , _liebling_. You are going to stay like that. You were so intent on staying put before, I’m sure you’ll have no problem managing it now.”

Fucking hell.

Caleb moves closer, ducking his head in, and Molly thinks he’s coming in for a kiss, but Caleb goes for his neck instead, kissing his way down until he reaches the juncture of neck and shoulder, and sucks a bruising kiss there.

It’s all Molly can do not to move, wrists twisting in the ropes behind him. A moan slips out of him as Caleb finishes, ending with a gentle nip. Unbidden, Molly’s hips twitch, and his moan turns into a whine when there’s nothing for his cock to touch at all. Occasionally, the tails of Caleb’s shirt front brush it, but that’s almost worse than nothing.

“Caleb, please-” He cuts off with a choked whimper as Caleb sits in front of him and starts petting up the insides of Molly’s thighs, ending up near his hips and back down to his knees, pointedly not touching Molly’s cock. “Caleb- _please_!”

“Please what, _schatz_?”

“Touch me-” Caleb’s mouth opens, and Molly realizes his mistake.

He’s made this mistake before.

“Touch my cock!” he quickly corrects. “Please- _please-_ ”

“Hmm,” Caleb hums consideringly. He lets his hands drift back up to Molly’s hips, thumbs sweeping over the soft, sensitive skin just below Molly’s hipbones. His smile turns wicked, and he lightly touches the head of Molly’s cock with a single fingertip. “How is this, _schatz_?”

He knows- _knows-_ that Caleb’s going to pull his finger away. He knows it with a surety that he has for little else. He loves Caleb dearly, but he’s a little shit when he wants to be, and right now he wants to be.

That doesn’t stop Molly from trying to buck forward against it, to get any kind of friction or touch he can.

The finger does in fact move away after a split second, and all Molly can really do is squirm, wrists tugging uselessly behind him. His tail is still going crazy, and while he wishes he could keep it still if only to spare his nipples, he knows that’s not really an option; the damned thing only stays put when it’s being held or tied down.

Oh...tail bondage. Now _there’s_ an idea for later.

“If you can keep your hips still, I will touch you more.” Caleb loosely wraps his fingers around the base of Molly’s cock, giving one loose, agonizingly-slow stroke up until his fingers are just below the head, then lets go.

Molly can’t even answer, just nodding and bracing himself, knowing Caleb would never make anything so easy as that.

And he’s right.

Caleb goes after him with a will, hands seemingly everywhere at once, and Molly’s thighs quiver with the effort of staying still, of not bucking forward into every slide of Caleb’s fingers over his length, of Caleb massaging lightly behind his balls, fingers once again tracing up and down his thighs.

It’s an overload of sensation, but it’s not enough- none of it is enough to be able to pull him over the edge. He’s close, but not so close that Caleb might drag him over by accident, and before long pleas start spilling out his mouth in place of the physical movement he’s trying to hold back.

“Caleb- _Caleb-_ gods, please- a bit more- I need- _nng-_ just- Caleb, _please_ -”

Eventually, even through his lust-addled mind, Molly realizes Caleb’s movements are slowing down, almost coming to a stop. His thighs are shaking with the effort of keeping still, but also with the effort of keeping the position.

“You have a choice- I can get you off right now-” Caleb gives Molly another slow stroke, dragging a cry from him. “Or, if you think you can wait a little longer, I can fuck you.”

Gods almighty. It always does something to him when Caleb talks like that, so matter-of-fact and crass. He wants to come- _badly-_ but knowing he could have Caleb in him-?

“ _You-_ ” he gasps. “I want you- in me- please.”

“Very well.” Caleb gives him a once over, brow wrinkled in thought. “Just a moment.” He collects the wayward memory foam pillow from earlier, along with a few others, and makes a mound of them, but pauses before bending Molly over them.

“I think perhaps we are done with these.” He reaches for one of the nipple clamps and Molly scrunches his eyes shut, wrists flexing. This is going to hurt; just because he enjoys it doesn’t change that fact.

There’s a light tug on one of the strings, but it pulls his tail forward rather than pulling his nipple up, and he quickly realizes that’s so Caleb can more-easily loosen the clamp. He shouts and writhes as it releases, blood flowing in all at once. The action is quickly followed with the other, and while he’s glad to be free of them for now, he knows they’re only going to be more sensitive when Caleb has him bent over.

Caleb takes a moment to rub over them with his thumbs, encouraging blood flow, and while Molly knows that’s what he’s doing, he thinks Caleb goes a little longer than strictly necessary. When Caleb’s satisfied, he helps Molly lean forward onto the pillows so they’re supporting his chest and shoulders, with his head extending beyond. Caleb asks him to widen his stance a little more, and Molly does with a whimper, though it flows into a moan when Caleb catches hold of his tail to remove the band on it.

He feels so deliciously vulnerable, ass in the air, hands bound, knees spread, just waiting for Caleb to come and fuck him. A shiver lights up his spine, causing the end of his tail to flick.

“Caleb- I need you.” He squirms as enticingly as he can, twisting his wrists in a show of helplessness.

“And you will have me.” There’s rustling behind him, but he can’t see Caleb from where he’s positioned.

“That better be the sound of you undressing-”

“Or what?” The mattress dips again behind him, Molly sucking in a breath as Caleb’s hands land on his ass, giving it a squeeze. “You will wave your tail at me in threat?”

Molly makes to have his tail take a swat at Caleb just to be contrary and yelps when Caleb grabs it out of the air.

“Perhaps instead of fucking you as planned I should spend some time playing with this,” Caleb says, giving a pointed tug on the base of Molly’s tail. “With you waving it around at me, I can only assume that it’s what you want me to pay attention to.”

“Gods, no, Caleb- I’m sorry, I didn’t- _please_ , fuck me-”

“Mmhm.” Caleb moves a little closer and lifts Molly’s tail to drape over his shoulder so it’s out of his way. There’s the sound of a bottle opening, and Molly wiggles happily. He knows that sound; he _loves_ that sound. That sound promises many fun things in his immediate future.

He’s wound so tight that he jumps with a quiet squeak at the first touch of a slicked fingertip over his hole. Caleb doesn’t stop, only putting a steadying hand on Molly’s hip, circling his finger gently until Molly’s squirming again.

“Patience, _liebling_ -”

“Easy for _you_ to say.”

Molly half-expects Caleb to retaliate for the sass in some way, but he doesn’t, just continues prepping Molly. He’s slow, and methodical, but Molly knows that’s not out of the ordinary- Caleb would do that even if Molly’d been on his best behavior. On top of being precise, Caleb is _thorough_ , unwilling to compromise Molly’s safety in any way.

While Molly greatly appreciates that, and while it’s one of the many things Molly loves about Caleb, right now he thinks it might be the death of him.

He wriggles in place, trying to lean back and bear down on Caleb’s fingers, trying to get more, but Caleb just pulls his hand back and waits for Molly’s wriggling to subside. It doesn’t take Molly long to realize though that depending on how much he wriggles, it barely manages to bump and drag his cock against the side of the pillow stack. He has no idea whether that’s better or worse than nothing at all, but he’s so desperate it doesn’t matter; he can’t stop his hips from swaying forward, from trying to get any kind of touch he can.

“If you continue to do that, I will stop what I’m doing and put you in a cock cage until I’m ready for you to come.”

It’s with a force of will that Molly stills the movement of his hips, stops trying to buck forward, and holds himself still while Caleb continues to work him open. The slick drag of Caleb’s fingers in and out keeps punching small sounds out of him, not quite begging, but a plea all the same. At one point Caleb’s fingers graze Molly’s prostate, pulling a yell out of him as he tenses, and Caleb, the bastard, does it again.

And again.

Molly shudders, shaking and close to being beyond caring about Caleb’s threat. Caleb asks him if he could come from just this, and while he wants to say no outright, he doesn’t know that it’s actually true; he’s never tried before.

“I- I don’t know- just- Caleb, please fuck me, please fuck me, _please-_ ”

“Shh-” Caleb’s fingers pull out and he hushes Molly again at Molly’s cry of dismay. “Just a moment, _schatz_ , I promise you’ll get what you want in just a moment. You’ve been very good.”

There’s the sound of the lube bottle again, opening then closing, the slick sound of skin-on-skin before one of Caleb’s hands is at Molly’s hip again, squeezing, and there’s the press of Caleb’s cock at his entrance.

“ _Finally_ -” Molly knows better than to try to lean back again, to try to urge Caleb faster; instead he does his best to brace and not move at all, to hold himself exactly in-place rather than letting himself be nudged forward. He wants Caleb to slam forward, to take what he wants, to be anything but gentle, but it’s not up to him.

It’s up to Caleb.

And Caleb delights in making Molly wait, in testing Molly’s will and patience, in driving Molly to the edge of what he thinks he can stand, then somehow pushing him past that until he’s a writhing, begging mess.

It’s _wonderful_.

It’s the matter of a few moments for Caleb to stop his forward press, hips up against Molly’s ass. Molly’s tail has already fallen off Caleb’s shoulder, moving to a more-comfortable position to the side instead of straight up, and Caleb doesn’t stop it as it wraps around his waist.

Molly’s seconds from begging again when Caleb pulls back before snapping his hips forward, pulling a grateful moan out of Molly.

“ _Yes_ -” Molly does his best to stay in place, to not move back to meet every thrust of Caleb’s hips, but it’s so _difficult_. Caleb’s been winding him up for over an hour now, and there’s very little Molly wants to do more than come; he knows though that if he pushes, Caleb isn’t above slowing or even stopping his own movements. Molly has no idea how he does it, how he has the patience for it.

“Caleb- _please_ can I move?” He knows his voice is strained, and he can’t stop twisting his wrists in the ropes, fingers flexing as he wishes he had something to hold onto.

The hands on his hips give a squeeze, and Molly lets out a sigh of relief when Caleb gasps out, “ _Ja_ , _schatz_ , you can.”

Letting out a shuddering breath, Molly finally lets himself move, pressing his shoulders down so he can lean back to meet Caleb’s thrusts, his tail squeezing around Caleb’s waist, trying to pull him closer.

As if Caleb could ever be close enough.

Once he’s allowed to move, Molly finds his restraint on a lot of things falls to the wayside, gasps and moans pulled out of him as Caleb pushes him closer to the edge again.

“Yes, Caleb, _please_ \- harder, like you mean it, I’m so- _aaa_!” Molly’s words get cut off as Caleb gets a firmer grip on Molly’s hips and drives drives forward at the perfect angle, knocking the breath right out of him.

Caleb’s memory practically gives him a fucking targeting system; once he finds the right spot he just keeps repeating the same movements, driving Molly closer and closer to the edge.

“Just- Caleb, _please_ -” Molly groans as Caleb snaps his hips forward again, and he’s so close- he’s _so close_ \- but he needs...he needs-

“Hand-” Molly manages to gasp out. “Caleb please, for the love of the gods, _touch me_ , I can’t-”

One of Caleb’s hands lets go of Molly’s hips and Molly sobs in relief when it then works its way around him to get hold of his cock. He wants to say thank you, to show how grateful he is, that he’s not taking it for granted, but the only word that he can seem to reliably get out at this point is ‘please’.

With Caleb’s hand on him finally, it’s a headlong rush, and Molly careens into his orgasm with a deep groan, shuddering as he keeps trying to buck forward into Caleb’s fist. Behind him Caleb lets out a similar noise as Molly tightening around him drags him over the edge as well.

For a moment they just lay there, catching their breath, but eventually Caleb withdraws, pulling one last moan out of Molly as he goes.

“How are you feeling, _schatz_?”

“ _Fuck_ -” Molly rolls to his side, stretching to the extent he can. “Fucking amazing, love, thank you.”

“You’re very welcome.” Caleb comes up behind him, petting down Molly’s arms before getting to his wrists and undoing the ropes there. Once Molly’s loose, Caleb helps him move his arms back around front, rubbing his thumbs over the imprints left on Molly’s wrists from the rope as Molly wiggles around until his back is supported by the pile of pillows.

“I think I’m going to want a very hot soak in the tub in a bit, but I need to wait until my knees re-solidify, first.”

Snorting, Caleb releases Molly’s wrists, crawling up the bed to sit next to him, gently taking hold of Molly’s chin to pull him into a kiss.

“I will take that as a compliment.”

“Mmhm, as well you might.” Molly snuggles closer, letting his arm drape over Caleb’s side, humming happily as Caleb pulls him closer, wrapping Molly up in his arms. The sex is of course amazing, but the cuddles afterward aren’t too shabby, either.

“Just give me a few minutes,” Molly says, nuzzling at Caleb’s collarbone. “And I’ll be good to go.”

“Take your time, _schatz_ , there is no rush.”

Molly sighs, and the feel of Caleb’s fingers carding through his hair lull him into a much-needed nap.


End file.
